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8th October 2016 @ 04:16

Reaction Scheme

 


Procedure

1.48 g (4.955 mmol, 1 eq) of 2-Chloro-6-hydrazinylpyrazine (product from reaction 2-4), were dissolved in 25 mL DCM to form a brown suspension/sludge. Approximately 1.9 g (5.7 mmol, 1.2 eq) of PhI(OAc)2 were added, and the solution was stirred under inert atmosphere. As the reaction proceded, the solution cleared and became redidish-brown. After stirring for 2 days, the solution was yellow.

 

Workup

The reaction was quenched with 25 mL saturated NaHCO3 solution, then transfered to a seperatory funnel, and diluted with 10 mL DCM. The organic layer was removed, and the aqueous layer was extracted with 20 mL DCM thrice. The organic layers were combined, and washed with 20 mL saturated NaHCO3, then washed with 20 mL brine. MgSO4 was added, and the solution was filtered. Solvent was removed via rotory evaporation and high vac.  The product was then left to sit in an open flask in the hood for 1 week, over which the product changed from light brown to red-brown. The product was dissolved again in DCM, transfered to another round bottom flask, rotory evaporated and placed on the hi vac to give a yield of 2.0541 g (6.9241 mmol, 139.7% yield).


InChI

InChI=1S/C12H9ClF2N4O/c13-10-6-16-7-11(18-10)19-17-5-8-1-3-9(4-2-8)20-12(14)15/h1-7,12H,(H,18,19)/b17-5+

to 

InChI=1S/C12H7ClF2N4O/c13-9-5-16-6-10-17-18-11(19(9)10)7-1-3-8(4-2-7)20-12(14)15/h1-6,12H


SMILES

ClC1=CN=CC(N([H])/N=C/C2=CC=C(OC(F)F)C=C2)=N1

to
 
ClC1=CN=CC2=NN=C(C3=CC=C(OC(F)F)C=C3)N21
Attached Files
TLC Reaction 3-3 Annotated.jpg
TLC Reaction 3-3.jpg
RXN 3-3 10-6-16.jpg
Reaction 3-3 GCMS.pdf
rxn3r3_CARBON_dmso.jcamp
rxn3r3_CARBON_dmso.pdf
rxn3r3_PROTON_cdcl3.jcamp
rxn3r3_PROTON_cdcl3.pdf
Comments
Re: (10-4-16) Synthesis of 5-chloro-3-(4-(difluoromethoxy)phenyl)-[1,2,4]triazolo[4,3-a]pyrazine [rxn 3-3] by Aaron Schankler
1st November 2016 @ 05:38
A discussion of the second order NMR splittings and distorted integrations can be found here. It was noted that before publication, better spectra will need to be recorded.

Link:
https://github.com/OpenSourceMalaria/OSM_To_Do_List/issues/454#issuecomment-257281225